Procaine
Title: Procaine
CAS Registry Number: 59-46-1
CAS Name: 4-Aminobenzoic acid 2-(diethylamino)ethyl ester
Additional Names: p-aminobenzoyldiethylaminoethanol; 2-diethylaminoethyl p-aminobenzoate
Molecular Formula: C13H20N2O2
Molecular Weight: 236.31
Percent Composition: C 66.07%, H 8.53%, N 11.85%, O 13.54%
Literature References: Benzoic acid derivative with anesthetic activity. Prepn: A. Einhorn, US 812554 (1906); idem, Ann. 371, 125 (1909); A. Einhorn, E. Uhlfelder, ibid. 131. CNS effects: C. G. Peterson, Anesthesiology 16, 976 (1955). Intravenous pharmacokinetics in humans: A. B. Seifen et al., Anesth. Analg. 58, 382 (1979). Clinical evaluation as anti-arrhythmic and cough suppressant during anesthesia: D. S. Thompson et al., Am. J. Surg. 138, 798 (1979). Stabilization of vascular smooth muscle in vitro: K. Kitamura et al., Drugs Exp. Clin. Res. 12, 773 (1986). Toxicity data: W. C. North, K. F. Urbach, J. Am. Pharm. Assoc. Sci. Ed. 45, 382 (1956); E. I. Goldenthal, Toxicol. Appl. Pharmacol. 18, 185 (1971).
Properties: Hygroscopic, anhydr plates, tablets from ligroin or ether, mp 61°. When freshly precipitated, one gram dissolves in 200 ml water. Sol in alc, ether, benzene, chloroform. LD50 in mice (mg/kg): 195 i.p.; 45 i.v. (North, Urbach).
Melting point: mp 61°
Toxicity data: LD50 in mice (mg/kg): 195 i.p.; 45 i.v. (North, Urbach)
 
Derivative Type: Dihydrate
CAS Registry Number: 6192-89-8
Properties: Needles from aq alc, mp 51°. Slightly bitter taste; applied to the tongue causes transitory numbing sensation.
Melting point: mp 51°
 
Derivative Type: Nitrate
CAS Registry Number: 6192-92-3
Molecular Formula: C13H20N2O2.HNO3
Molecular Weight: 299.32
Percent Composition: C 52.16%, H 7.07%, N 14.04%, O 26.73%
Properties: Crystals, mp 100-102°. Sol in water, alcohol. The aq soln is neutral. Particularly useful with silver nitrate because no precipitate forms.
Melting point: mp 100-102°
 
Derivative Type: Butyrate
CAS Registry Number: 136-55-0
Trademarks: Probutylin (Rorer)
Molecular Formula: C13H20N2O2.C4H8O2
Molecular Weight: 324.42
Percent Composition: C 62.94%, H 8.70%, N 8.63%, O 19.73%
Properties: Hygroscopic crystals. Soluble in water, alcohol, vegetable oils.
 
Derivative Type: Hydrochloride
CAS Registry Number: 51-05-8
Trademarks: Anestil; Enpro (Kobayashi); Gero (URPAC); Jenacaine; Medaject (Neda); Naucaine; Neocaine; Novocain (Sanofi Winthrop); Omnicain (Daiichi); Planocaine (M & B); Rocain (Fuso); Syntocain (Sintetica)
Molecular Formula: C13H20N2O2.HCl
Molecular Weight: 272.77
Percent Composition: C 57.24%, H 7.76%, N 10.27%, O 11.73%, Cl 13.00%
Properties: Crystals. Six-sided plates, monoclinic or triclinic. mp 153-156°. Numbing taste. Stable in air. One gram dissolves in 1 ml water and in 30 ml alcohol. Slightly sol in chloroform. Almost insol in ether. The pH of a 0.1M aq soln is 6.0. Aq solns may be sterilized by boiling. LD50 in mice (mg/kg): 660 ± 60 s.c. (Goldenthal).
Melting point: mp 153-156°
Toxicity data: LD50 in mice (mg/kg): 660 ± 60 s.c. (Goldenthal)
 
Therap-Cat: Anesthetic (local).
Therap-Cat-Vet: Anesthetic (local).
Keywords: Anesthetic (Local).

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